Biantennary oligoglycines and glyco-oligoglycines self-associating in aqueous medium

• Svetlana V. Tsygankova,
• Alexander A. Chinarev,
• Alexander B. Tuzikov,
• Nikolai Severin,
• Alexey A. Kalachev,
• Juergen P. Rabe,
• Alexandra S. Gambaryan and
• Nicolai V. Bovin

Beilstein J. Org. Chem. 2014, 10, 1372–1382, doi:10.3762/bjoc.10.140

• chemical shifts was calibrated against the signals of residual protons of solvents (CDCl3: δ 7.26 ppm; DMSO-d6: δ 2.50 ppm; D2O: δ 4.75 ppm). Mass-spectra were recorded on the time-of-flight spectrometer Vision-2000 (Thermo Bioanalysis, UK) with MALDI with 2,6-dihydroxybenzoic acid as reference. Raman

Glycosystems in nanotechnology: Gold glyconanoparticles as carrier for anti-HIV prodrugs

• Fabrizio Chiodo,
• Marco Marradi,
• Javier Calvo,
• Eloisa Yuste and
• Soledad Penadés

Beilstein J. Org. Chem. 2014, 10, 1339–1346, doi:10.3762/bjoc.10.136

• paragraph). The ester derivatives were not detected in the EtOH washings after the GNPs precipitation (by MALDI–MS and 1H NMR) indicating that practically all the drug conjugates were linked on the gold surface. Drug quantification and release of the drug from GNPs We studied the stability of the GNPs

Automated solid-phase peptide synthesis to obtain therapeutic peptides

• Veronika Mäde,
• Sylvia Els-Heindl and
• Annette G. Beck-Sickinger

Beilstein J. Org. Chem. 2014, 10, 1197–1212, doi:10.3762/bjoc.10.118

• major prerequisite for the success of SPPS, both with respect to analytics and preparative purification [25]. Furthermore, high-quality mass spectrometry (MS) with soft ionization techniques such as MALDI–TOF (matrix-assisted laser desorption ionization – time of flight) and ESI (electrospray ionization

Solid-phase-supported synthesis of morpholinoglycine oligonucleotide mimics

• Tatyana V. Abramova,
• Sergey S. Belov,
• Yulia V. Tarasenko and
• Vladimir N. Silnikov

Beilstein J. Org. Chem. 2014, 10, 1151–1158, doi:10.3762/bjoc.10.115

• at 30 °C. Chemical shifts (δ) are reported in ppm relative to TMS signals. Coupling constants J are reported in Hertz. MALDI–TOF mass spectra were registered on an Autoflex III mass spectrometer (Bruker Daltonics, Germany) using 2,5-dihydroxybenzoic acid as a matrix (MALDI–TOF) in positive or

• (app. t, J = 10.3 Hz, 1H, H3), 2.01 (app. t, J = 10.6 Hz, 1H, H5), 1.77 (s, 3H, СН3-Thy), 1.37 (s, 9H, CH3-Boc); MALDI–TOFMS (m/z): [M + H]+ calcd for C17H27N4O7, 399.19; found, 399.77; [M + Na]+ calcd for C17H26N4NaO7, 421.17; found, 421.64. See Supporting Information File 1 for the synthetic scheme

• , 1H, H5), 2.75–2.64 (m, 2H, NH2CH2), 1.81 (d, J = 0.8 Hz, 3H, CH3), 1.39 (dd, J = 11.1, 10.0 Hz, 1H, H3), 1.35–1.30 (dd, J = 11.6, 10.6 Hz, 1H, H5); MALDI–TOFMS (m/z): [M – Tr + 2H]+ (the Tr protective group was removed during the sample preparation) calcd for C10H17N4O3 241.13; found, 241.45

Novel indolin-2-one-substituted methanofullerenes bearing long n-alkyl chains: synthesis and application in bulk-heterojunction solar cells

• Irina P. Romanova,
• Andrei V. Bogdanov,
• Inessa A. Izdelieva,
• Vasily A. Trukhanov,
• Gulnara R. Shaikhutdinova,
• Dmitry G. Yakhvarov,
• Shamil K. Latypov,
• Vladimir F. Mironov,
• Vladimir A. Dyakov,
• Ilya V. Golovnin,
• Dmitry Yu. Paraschuk and
• Oleg G. Sinyashin

Beilstein J. Org. Chem. 2014, 10, 1121–1128, doi:10.3762/bjoc.10.111

• fullerene. UV–vis, IR, and NMR spectroscopy confirmed their structure. The composition was established by MALDI–TOF mass spectrometry. Optical absorption, electrochemical properties and solubility of AIMs Figure 2 compares a typical optical absorption spectrum of AIMs with those of PCBM and pristine

• Ultraflex III MALDI TOF/TOF SYSTEM» apparatus. NMR experiments were carried out with a Bruker AVANCE-600 spectrometer (14.1 T) equipped with a pulsed gradient unit capable of producing magnetic field pulse gradients in the z-direction of 56 G·cm−1. All spectra were acquired in a 5 mm inverse probehead

Towards allosteric receptors – synthesis of β-cyclodextrin-functionalised 2,2’-bipyridines and their metal complexes

• Christopher Kremer,
• Gregor Schnakenburg and
• Arne Lützen

Beilstein J. Org. Chem. 2014, 10, 814–824, doi:10.3762/bjoc.10.77

• )]PF6, and [Zn(22)(1)](OTf)2 as evidenced by MALDI mass spectrometry and NMR spectroscopy (Figure 6 and Figure 7). Hence, zinc(II) ions or their complexes with a single, sterically demanding phenanthroline ligand like 22 as well as a similar [Cu(22)]+ complex were all found to be good effectors for

• : carbon, red: oxygen, blue: nitrogen, yellow: sulfur, white: hydrogen). MALDI mass spectrum (sample prepared from a 1:1 mixture of CuPF6 and 2 in benzene/acetonitrile (1:1) using DCTB (trans-2-[3-(4-tert-butylphenyl)-2-methyl-2-propenylidene]malononitrile) as matrix). Aromatic region of the 1H NMR spectra

• , benzene-d6/acetonitrile-d3 1:1) of a) 1, b) [Zn(22)(1)](OTf)2, and c) 22. Arrows indicate signal shifts upon formation of the heteroleptic complex. MALDI–TOF mass spectrum (sample prepared from of a 1:1:1 mixture of CuPF6, 22, and 1 in benzene/acetonitrile (1:1) using DCTB as matrix). Off- (open) and on

Staudinger ligation towards cyclodextrin dimers in aqueous/organic media. Synthesis, conformations and guest-encapsulation ability

• Malamatenia D. Manouilidou,
• Yannis G. Lazarou,
• Irene M. Mavridis and
• Konstantina Yannakopoulou

Beilstein J. Org. Chem. 2014, 10, 774–783, doi:10.3762/bjoc.10.73

• dissolution of 2 or 3 were observed evidently due to secondary reactions leading to a lower yield for the ligation step. Monomer 4 and dimer 6 displayed a single 31P NMR signal at 35.2 ppm and the correct mass in MALDI–TOF MS. Reaction of 4 with mono(6-15N-amino-6-deoxy)-β-CD under typical amide coupling

• gratefully acknowledged. A scholarship to M.D.M. by NCSR “Demokritos” is gratefully acknowledged. We also thank Mr. A. R. L. Marouvo Gonçalves of our group for preparing NDTAM·HCl. Istituto di Ricerche Chimiche e Biochimiche "G. Ronzoni" Milano, Italy, is also acknowledged for the MALDI–TOF measurements.

Thermodynamically stable [4 + 2] cycloadducts of lanthanum-encapsulated endohedral metallofullerenes

• Yuta Takano,
• Yuki Nagashima,
• M. Ángeles Herranz,
• Nazario Martín and
• Takeshi Akasaka

Beilstein J. Org. Chem. 2014, 10, 714–721, doi:10.3762/bjoc.10.65

• spectroscopic methods such as MALDI–TOF mass, optical absorption, and NMR spectroscopy. The [4 + 2] adducts of La2@C80 (3a,b, and 4a,b) and La@C82 (5b), respectively, retain diamagnetic and paramagnetic properties, as confirmed by EPR spectroscopy. Dynamic NMR measurements of 4a at various temperatures

• the cycloadducts (3a,b and 4a,b). The reactions were traced using HPLC analyses (Figure 1), and formation of the resulting [4 + 2] adducts was confirmed by matrix-assisted laser desorption ionization (MALDI) TOF mass spectrometry (Figure 2), which shows the molecular ion peaks for the corresponding

• compounds in HPLC. The mixture of 3a and 4a was first separated from the unreacted starting materials and byproducts through one-step HPLC separation. The MALDI–TOF mass spectra of 3a and 4a showed single peaks attributed to the molecular ion peak of the target molecule, La2@C80C2H4C6H4, at 1342 m/z (Figure

End-group-functionalized poly(N,N-diethylacrylamide) via free-radical chain transfer polymerization: Influence of sulfur oxidation and cyclodextrin on self-organization and cloud points in water

• Sebastian Reinelt,
• Daniel Steinke and
• Helmut Ritter

Beilstein J. Org. Chem. 2014, 10, 680–691, doi:10.3762/bjoc.10.61

• functionalization is supported by 1H NMR-, SEC-, FTIR- and MALDI–TOF measurements. Keywords: chain-transfer polymerization; cyclodextrins; end-group functionalization; host–guest interaction; lower critical solution temperature (LCST); poly(N,N-diethylacrylamide); Introduction Supramolecular chemistry was first

• Table 1. Exemplarily, Figure 1 shows a section of the MALDI–TOF spectrum of polymer 8b confirming a high degree of 4-tert-butylphenol end-group functionalization. Just single series of peaks with a peak separation of 127.1 which corresponds to the mass of DEAAm plus the proposed end-group (224.1) and

• accomplished by oxidation with hydrogen peroxide in analogy to literature [11]. As expected, the MALDI–TOF mass spectrum for 8bOx showed only one series of peaks, which was shifted by 16 Dalton in comparison to the origin series of peaks (see Figure 3). The FTIR spectrum showed a decrease of transmission at a

Rapid pseudo five-component synthesis of intensively blue luminescent 2,5-di(hetero)arylfurans via a Sonogashira–Glaser cyclization sequence

• Fabian Klukas,
• Alexander Grunwald,
• Franziska Menschel and
• Thomas J. J. Müller

Beilstein J. Org. Chem. 2014, 10, 672–679, doi:10.3762/bjoc.10.60

• analyzed by MALDI–TOF mass spectrometry indicating the formation of oligomers with m/z = 422 to 1046. We could efficiently suppress this oligo- and polymerization by increasing the amount of solvent, i.e. by dilution (Table 1, entries 9–13). Additionally increasing the concentration of KOH and water also

Tuning the interactions between electron spins in fullerene-based triad systems

• Maria A. Lebedeva,
• Thomas W. Chamberlain,
• E. Stephen Davies,
• Bradley E. Thomas,
• Martin Schröder and
• Andrei N. Khlobystov

Beilstein J. Org. Chem. 2014, 10, 332–343, doi:10.3762/bjoc.10.31

• [22] and was reacted with [60]fulleropyrrolidine 9 to give the benzyl ester protected compound 11 in 68% yield. Subsequent deprotection of 11 by CF3SO3H yielded the insoluble product 12 that precluded characterisation by solution based methods. However, MALDI–MS of 12 showed a molecular ion peak with

• solubility, but MALDI–MS (m/z 821) and IR spectroscopy (carbonyl stretch at 1733 cm−1) confirm the assigned structure. The dicyclohexylcarbodiimide (DCC) assisted acid–amine coupling reaction between 15 and [70]fulleropyrrolidine 10 resulted in the formation of the desired asymmetric triad 5, which displayed

• . 1H and 13C NMR spectra were obtained using Bruker DPX 300, Bruker DPX 400, Bruker AV(III) 400 or Bruker AV(III) 500 spectrometers. Mass spectrometry was carried out using a Bruker microTOF spectrometer and a Bruker ultraFlexIII MALDI–TOF spectrometer using trans-2-[3-(4-tert-butylphenyl)-2-methyl-2

Synthesis of nucleotide–amino acid conjugates designed for photo-CIDNP experiments by a phosphotriester approach

• Tatyana V. Abramova,
• Olga B. Morozova,
• Vladimir N. Silnikov and
• Alexandra V. Yurkovskaya

Beilstein J. Org. Chem. 2013, 9, 2898–2909, doi:10.3762/bjoc.9.326

• “Proteomics”, Russian Academy of Sciences, on an Autoflex III mass spectrometer (Bruker Daltonics, Inc.) using 2,5-dihydroxybenzoic acid as a matrix (MALDI–TOF) in positive or negative mode. Compound 22 was synthesized according to the published method [32]. Trifluoroacetamido-NH-tryptophan was obtained as

• ); MALDI–TOFMS (m/z): [M + H]+ calcd for C25H30ClN5O10P, 626.14; found, 626.05; [M + Na]+ calcd for C25H29ClN5NaO10P, 648.12; found, 648.04. General phosphorylation procedure Compound 10, 12, 15, 23, or 26 (0.2 mmol) and 1,2,4-triazole (0.08 g, 1.2 mmol) were coevaporated with Py (3 × 1 mL), dissolved in

• , H3’), 4.05–4.00 (m, 2H, OCH2CH2OP), 3.98–3.92 (m, 2H, OCH2CH2OP), 3.70 (t, J = 5.3, 2H, NHCH2CH2O), 3.68–3.64 (m, 2H, H5’5”), 3.59 (t, J = 5.3, 2H, NHCH2CH2O), 2.54–2.43 (m, 1H, H2’), 2.34–2.24 (m, 1H, H2”); MALDI–TOFMS (m/z): [M + H]+ calcd for C28H32N6O10P, 643.19; found, 643.19; [M + Na]+ calcd

Oligomeric epoxide–amine adducts based on 2-amino-N-isopropylacetamide and α-amino-ε-caprolactam: Solubility in presence of cyclodextrin and curing properties

• Julian Fischer and
• Helmut Ritter

Beilstein J. Org. Chem. 2013, 9, 2803–2811, doi:10.3762/bjoc.9.315

• spectrometry (ESIMS) was conducted on a Bruker maXis 4G mass spectrometer and matrix-assisted laser desorption-ionization time-of-flight mass spectrometry (MALDI-TOF-MS) on a Bruker Dalomics Ultraflex 1 mass spectrometer. Melting points were obtained using a Büchi Melting Point B-545 apparatus at a heating

Synthesis of homo- and heteromultivalent carbohydrate-functionalized oligo(amidoamines) using novel glyco-building blocks

• Felix Wojcik,
• Sinaida Lel,
• Alexander G. O’Brien,
• Peter H. Seeberger and
• Laura Hartmann

Beilstein J. Org. Chem. 2013, 9, 2395–2403, doi:10.3762/bjoc.9.276

• -CONH2 (14): Compound 14 (30 mg, 16.2 μmol) was obtained as white hygroscopic powder after cleavage from the resin, precipitation into diethyl ether and deactylation with a yield of 81%. MALDI–TOF–MS: [M + Na]+ calcd for C75H135N13O33S3Na, 1864.83 (monoisotopic); found, 1864.63; RP-HPLC analysis 5% to 95

• deactylation compound 15 (11 mg, 5.6 μmol) was obtained as white hygroscopic powder with 28% yield. MALDI–TOF–MS: [M + H]+ calcd for C79H140N11O40S3, 1978.84 (monoisotopic); found, 1979.06; [M + Na]+ calcd for C79H139N11O40S3Na, 2000.82 (monoisotopic); found, 2000.88; [M + K]+ calcd for C79H139N11O40S3K

• deactylation in solution, the crude material was purified via preparative RP-HPLC (5 to 50% MeCN in 30 min) and freezed-dried. Compound 16 (12.6 mg, 4.2 μmol) was obtained as white hygroscopic powder with 21% yield. MALDI–TOF–MS: [M + Na]+ calcd for C124H217N23O49S6Na, 3027.34 (monoisotopic); found, 3027.71

One-pot sequential synthesis of isocyanates and urea derivatives via a microwave-assisted Staudinger–aza-Wittig reaction

• Diego Carnaroglio,
• Katia Martina,
• Giovanni Palmisano,
• Andrea Penoni,
• Claudia Domini and
• Giancarlo Cravotto

Beilstein J. Org. Chem. 2013, 9, 2378–2386, doi:10.3762/bjoc.9.274

• determined using MALDI-TOF mass spectra (Bruker Ultraflex TOF mass spectrometer). General procedures Representative procedure for alkyl isocyanate synthesis from alkyl azide: PS-PPh2 (0.477 mmol) was added to a solution of alkyl azide (0.318 mmol) in MeCN (1.5 mL). The mixture was irradiated by MW for 1.5 h

Bis(benzylamine) monomers: One-pot preparation and application in dendrimer scaffolds for removing pyrene from aqueous environments

• Olivia N. Monaco,
• Sarah C. Tomas,
• Meghan K. Kirrane and
• Amy M. Balija

Beilstein J. Org. Chem. 2013, 9, 2320–2327, doi:10.3762/bjoc.9.266

• dendrimers 11–13 (Scheme 3), which were successfully purified by size exclusion chromatography (SEC). The products were determined to be >90% pure through 1H NMR spectroscopy and their molecular weights were confirmed by MALDI–TOF. The resulting novel dendrimers contained six amino groups within the interior

• compounds 3a–g, 4a–h,6–8, and 11–13, and pyrene fluorescence spectral data. Acknowledgements We thank Tom Carberry and Marcus Weck from New York University for their help in obtaining the MALDI–TOF data and the Dean’s Office at Fordham University for its generous financial support. The Q-Tof Ultima mass

• spectrometer (University of Illinois at Urbana-Champaign) was purchased in part with a grant from the NSF, Division of Biological Infrastructure (DBI-0100085) and the Bruker MALDI–TOF/TOF UltrafleXtreme MS Spectrometer (New York University) was acquired through the support of the NSF (CHE-0958457).

Gold-catalyzed glycosidation for the synthesis of trisaccharides by applying the armed–disarmed strategy

• Abhijeet K. Kayastha and
• Srinivas Hotha

Beilstein J. Org. Chem. 2013, 9, 2147–2155, doi:10.3762/bjoc.9.252

• resolution mass spectroscopy (HRMS) was performed on ABI–MALDI–TOF using TiO2 as the solid matrix. Compound characterization data Characterization data for compound 15j [38]: [α]D25 +28.2 (CHCl3, c 1.00); 1H NMR (200.13 MHz, CDCl3) δ 1.10–2.15 (m, 10H), 2.40 (s, 1H), 3.65–4.12 (m, 6H), 4.59 (s, 2H), 4.60

• (ABq, J = 12.6 Hz, 2H), 4.71 (ABq, J = 10.6 Hz, 2H), 4.76 (s, 2H), 5.56 (d, J = 1.8 Hz, 1H), 7.13–7.42 (m, 20H); 13C NMR (50.32 MHz, CDCl3) δ 22.7, 22.7, 25.0, 37.6, 38.2, 69.3, 71.9, 72.1, 72.3, 73.3, 74.1, 75.0, 75.2, 75.2, 75.5, 80.0, 84.6, 94.0, 127.3–128.3, 138.4, 138.5, 138.5, 138.5; HRMS (MALDI

• MHz, CDCl3) δ 55.4, 65.6, 66.6, 69.0, 69.1, 69.8, 70.6, 71.3, 71.7, 71.7, 71.7, 71.7, 72.2, 72.7, 73.2, 74.2, 74.6, 74.8, 74.9, 74.9, 75.0, 79.2, 80.2, 98.1, 98.2, 98.4, 127.2–129.8, 133.1, 133.3, 133.5, 138.3, 138.3, 138.4, 138.4, 138.6, 138.6, 138.7, 165.3, 165.4, 165.5; HRMS (MALDI–TOF, m/z): [M

Straightforward synthesis of a tetrasaccharide repeating unit corresponding to the O-antigen of Escherichia coli O16

• Manas Jana and
• Anup Kumar Misra

Beilstein J. Org. Chem. 2013, 9, 1757–1762, doi:10.3762/bjoc.9.203

• COCH3), 18.1 (CCH3); MALDI–MS: 1462.5 [M + Na]+; Anal. calcd for C76H85N3O25: C, 63.37; H, 5.95%; found: C, 63.20; H, 6.18%. p-Methoxyphenyl (β-D-galactofuranosyl)-(1→6)-(α-D-glucopyranosyl)-(1→3)-(α-L-rhamnopyranosyl)-(1→3)-2-acetamido-2-deoxy-α-D-glucopyranoside (1): Similar as described in [21]. To a

Controlled synthesis of poly(3-hexylthiophene) in continuous flow

• Helga Seyler,
• Jegadesan Subbiah,
• David J. Jones,
• Andrew B. Holmes and
• Wallace W. H. Wong

Beilstein J. Org. Chem. 2013, 9, 1492–1500, doi:10.3762/bjoc.9.170

• 3 (see Table 1 for experimental data). MALDI mass spectrum of low-molecular-weight preparation (GPC, Mn = 6.2 kg/mol) of P3HT in continuous flow. Signals corresponding to polymer chains with o-tolyl/H, H/H and Br/H end groups were observed. Plot of number-average molecular weight, Mn, versus monomer

• telescoped synthesis of P3HT from 2,5-dibromo-3-hexylthiophene (1) in flow.a Solar cell data for devices containing various P3HT samples.a Supporting Information Supporting Information File 386: Synthetic procedures for batch reactions, characterization of P3HT samples including NMR and MALDI-TOF spectra

A simple, enaminone-based approach to some bicyclic pyridazinium tetrafluoroborates

• František Josefík,
• Markéta Svobodová,
• Valerio Bertolasi and
• Petr Šimůnek

Beilstein J. Org. Chem. 2013, 9, 1463–1471, doi:10.3762/bjoc.9.166

• corrected. MALDI HRMS were measured using a MALDI LTQ Orbitrap XL (Thermo Fisher Scientific) with DCTB as the matrix dissolved in acetonitrile. The crystal data of all the compounds were collected at room temperature using a Nonius Kappa CCD diffractometer with graphite monochromated Mo Kα radiation. The

Linkage of α-cyclodextrin-terminated poly(dimethylsiloxanes) by inclusion of quasi bifunctional ferrocene

• Helmut Ritter,
• Berit Knudsen and
• Valerij Durnev

Beilstein J. Org. Chem. 2013, 9, 1278–1284, doi:10.3762/bjoc.9.144

• group and the Si–H bond of the starting materials are absent, as expected. The MALDI–TOF spectra of the modified poly(dimethylsiloxanes) 4 and 5 show terminally substituted products of various chain lengths, wherein the distance of 74 g/mol between the mass signals exactly corresponds to one

• -toluenesulfonyl)-6-deoxy)-α-cyclodextrin (α-tosyl-CD), mono-(6-N-allylamino)-6-deoxy)-α-cyclodextrin (AAm-α-CD) and mono-((6-N-allylamino)-6-deoxy)-peracetylated-α-cyclodextrin (AAm-Ac-α-CD) [21] were synthesized according to the literature. MALDI–TOF mass spectra were recorded with a Bruker Ultraflex time-of

• ), 4.78 (m, 12H), 5.06 (m, 12H), 5.55 (m, 12H); MALDI–TOF–MS m/z: 3962.58 [M + Na]+ for n = 12. Complexation reactions Complexation of α-CD-disiloxane (4) with ferrocene: α-CD-disiloxane (100 mg, 0.015 mmol) is dissolved in a solution of ferrocene (2.8 mg, 0.015 mmol) and 2.0 mL of chloroform and stirred

Synthesis, photophysical and electrochemical characterization of terpyridine-functionalized dendritic oligothiophenes and their Ru(II) complexes

• Amaresh Mishra,
• Elena Mena-Osteritz and
• Peter Bäuerle

Beilstein J. Org. Chem. 2013, 9, 866–876, doi:10.3762/bjoc.9.100

• oligothienylene-ethynylene dendrons and their corresponding terpyridine-based ligands. Their complexation with Ru(II) led to interesting novel metallodendrimers with rich spectroscopic properties. All new compounds were fully characterized by 1H and 13C NMR, as well as MALDI–TOF mass spectra. Density functional

• , MALDI–TOF-mass spectrometry and elemental analysis as well as by cyclic voltammetry and UV–vis spectroscopy. Electronic absorption and emission properties. One of our goals was to study electronic communication between the core metal complex and the attached oligothiophene dendron as a function of

• MALDI–TOF mass spectra on a Bruker Daltonic Reflex III (dithranol as the matrix). Iodinated dendrons 6 and 7 were prepared according to literature [42]. Photophysical measurements. Optical measurements were carried out in one centimeter cuvettes with Merck Uvasol grade solvents. Absorption spectra were

Superstructures of fluorescent cyclodextrin via click-reaction

• Arkadius Maciollek,
• Helmut Ritter and
• Rainer Beckert

Beilstein J. Org. Chem. 2013, 9, 827–831, doi:10.3762/bjoc.9.94

• and Discussion The water-soluble fluorescent cyclodextrin was synthesized via copper-catalyzed cycloaddition (Scheme 1). The existence of the resulting product was confirmed by MALDI–TOF spectrometry, 1H NMR and IR spectroscopy. The formation of host–guest structures between the thiazole functionality

• -of-flight mass spectrometry (MALDI–TOFMS) was performed on a Bruker Ultraflex TOF mass spectrometer. Ions were formed with a pulsed nitrogen laser (25 Hz, 337 nm) and the molecular masses were recorded in linear mode. 2,5-Dihydroxybenzoic acid (DBH) in acetonitrile/water was used as a matrix. Mass

• , OH), 3.75–3.53 (br, 28H, CH), 2.22 (br, 3H, CH3) ppm; IR: 3301 (OH), 2923 (C-H), 1653 (C=C), 1548 (ring vibr.), 1329 (OH), 1153 (COH), 1078 (COC), 1027 (COH) cm−1; MS (MALDI–TOF) (acetonitrile/water 1:10): m/z = 1412 [M + Na]+. 1H NMR-ROESY spectrum of the modified CD 3. UV–vis spectrum of 3 (4 × 10

End-labeled amino terminated monotelechelic glycopolymers generated by ROMP and Cu(I)-catalyzed azide–alkyne cycloaddition

• Ronald Okoth and
• Amit Basu

Beilstein J. Org. Chem. 2013, 9, 608–612, doi:10.3762/bjoc.9.66

• -methoxybenzylamine derivative 7 was prepared to facilitate characterization of the polymer by MALDI–ToFMS analysis (see Supporting Information File 1). Analysis of the MALDI spectra of polymer 7 showed incorporation of the end groups and the uniform interpeak distance confirmed the uniform incorporation of the Teoc

• terminus. The molecular data for 7 obtained by MALDI was in agreement with that obtained from GPC and NMR analysis of polymer 6 (see Supporting Information File 1). Due to its high conversion and functional-group tolerance the copper(I)-promoted azide–alkyne click reaction (CuAAC) has become a powerful

• . Supporting Information The Supporting Information contains detailed experimental procedures and characterization data for small molecules and polymers, including polymer GPC and MALDI data, and NMR spectra. Supporting Information File 176: Experimental procedures and characterization data. Acknowledgements

Synthesis and testing of the first azobenzene mannobioside as photoswitchable ligand for the bacterial lectin FimH

• Vijayanand Chandrasekaran,
• Katharina Kolbe,
• Femke Beiroth and
• Thisbe K. Lindhorst

Beilstein J. Org. Chem. 2013, 9, 223–233, doi:10.3762/bjoc.9.26

• NMR techniques (1H/1H COSY and 1H/13C HSQC). IR spectra were measured with a Perkin Elmer FT-IR Paragon 1000 (ATR) spectrometer. ESI mass spectra were recorded on an Esquire-LC instrument from Bruker Daltonics. MALDI-TOF mass spectra were recorded on a Bruker Biflex III instrument with 19 kV

• ), 98.7 (C-1), 75.2 (C-5), 70.6 (C-3), 69.9 (C-2), 66.6 (C-4), 60.9 (C-6); UV, λmax: 347 nm; ε = 25907 ± 529 L × mol−1 × cm−1; IR (ATR) : 3337, 2920, 1599, 1584, 1496, 1227 cm−1; MALDI-TOFMS (m/z): [M + H]+ calcd for 361.36; found, 361.21; anal. calcd for C18H20N2O6: C, 59.99; H, 5.59; N, 7.77; found: C

• , 2927, 1599, 1231, 1007, 685 cm−1; MALDI-TOFMS (m/z): [M + Na]+ calcd for C24H30N2O11, 545.18; found, 545.17; UV, λmax: 339 nm, ε = 14776 ± 729 L × mol−1 × cm−1; anal. calcd for C24H30N2O11 × 1.1 H2O: C, 52.11; H, 6.09; N, 5.07; found: C, 52.04; H, 5.79; N, 5.06. NMR-spectroscopic data for (Z)-2. 1H NMR